1. Field of the Invention
The field of the invention relates to heterocyclic organic compounds identified as 1-thia-3-aza-4-ones.
2. Description of the Prior Art
In the prior art, Surrey, J. Am. Chem. Soc. 69, 2911-2912 (1947), teaches the preparation of 4-thiazolidones by the reaction of thioglycolic acid with Schiff bases. This reference discloses no utilities for the compounds prepared as described therein.
Also in the prior art, Troutman, et al., J. Am. Chem. Soc. 70, 3436-3439 (1948), describe methods of synthesizing 2-aryl-3-alkyl- or 2-hetero-3-alkyl-4-thiazolidones, alleged to possess anticonvulsant activity.
Another prior art reference is Pennington et al., J. Am. Chem. Soc. 75, 109-114 (1953), which teaches the preparation of 2-substituted-4-thiazolidones, alleged to possess in vitro antitubercular activity.
Also in the prior art is Surrey et al., J. Am. Chem. Soc. 76, 578-580 (1954), which teaches the preparation of some 2-aryl-4-thiazolidones, alleged to possess significant amebicidal activity (Endamoeba criceti) when tested in hamsters.
Another prior art reference is that of Singh, J. Indian Chem. Soc., 595-597 (1976), which teaches the synthesis of a number of 5-methyl-3-aryl-2-arylimino-4-thiazolidinones, which, together with the acetoxymercuri derivatives thereof, are alleged to possess fungicidal activity against Alternaria solani, as the test organism.
Yet another prior art reference is Japanese Pat. No. 48-17276, which is directed to the manufacture of thiazolidone derivatives bearing a 2-pyridyl moiety in the molecular structure. The compounds are alleged to have central nervous system inhibiting activity.
Still another prior art reference is U.S. Pat. No. 4,017,628 (Apr. 12, 1977), which is directed to the treatment of mange using a 2-pyridyl substituted thiazolidinone compound.
Also in the prior art is Jadhav et al., J. Indian Chem. Soc. 55, 424-426 (1978), which teaches the preparation of some 2-methyl-2-(2-hydroxy-4,5-dimethylphenyl)-3-aryl-4-thiazolidinones, alleged to be inhibitory at 100 ppm. against Helmynthosporium appatarnae. This compound showed no activity in our tests.
Another reference is identified by Derwent No. 68466B/38 *EP-4-129 (published Sept. 19, 1979), and is directed to 2,3-disubstituted thiazolidinone-4 derivatives, alleged to be useful as herbicides, plant growth regulants, pesticides, fungicides, algicides, and antivirals.
Another reference in the art is U.S. Pat. No. 4,148,899 (Apr. 10, 1979), which is directed to ((5-nitro-2-thiazolyl)thio)-polyhalogenated pyridines, alleged to exhibit activity against fungi and bacteria. The compounds are alleged to be useful for incorporation into materials which are subject to fungal attack, e.g., latex and alkyl paint films, wood and wooden products. The compounds of this reference differ from those of the above-identified application in that the thiazole ring is joined to the pyridine ring via a sulfur atom, and further, the thiazole ring contains no carbonyl moiety.